Book Luxury Vacation Rentals in New Eastside

Award-winning homes from £98

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Home spotlights in New Eastside

Easel And Brush

Easel And Brush

  • 5 guests

  • 2 bedrooms

Near North, Chicago

If you’re visiting Chicago and you're interested in art, then the chic River North neighbourhood is the perfect place to stay. The area is now the city’s art and design quarter, with the highest concentration of galleries in the US after Manhattan.

Panorama Place

Panorama Place

  • 6 guests

  • 3 bedrooms

South Loop, Chicago

Chicago is laid out at your feet thanks to the floor-to-ceiling windows of this home. Whether you're watching TV in the white living space, cooking up a feast in the pine kitchen or waking up on the memory foam mattresses in the bedrooms, the skyline is visible.

Monday Night

Monday Night

  • 3 guests

  • 1 bedrooms

South Loop, Chicago

Convenience is key at this stylish apartment in Chicago’s trendy River North neighbourhood. From the moment you wake up in your plush, king-size bed you'll take in sprawling city views from the floor-to-ceiling windows.

Chicago Morning

Chicago Morning

  • 8 guests

  • 4 bedrooms

Printer's Row, Chicago

Initially designed by an architect for their family, this incredible Chicago condo has been featured in magazines and even TV commercials. Located in the heart of downtown Chicago, this home is central to the sights and activities of the area, and also boasts an incredible green, real grass rooftop terrace with views that span across the south, east, and west of the city.


We selected the top 3% holiday homes in New Eastside Vacation Rentals

Explore the 46 most perfect homes in our collection

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Most popular homes in New Eastside

Gilded Frame

Gilded Frame

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Slice Of Sky

Slice Of Sky

  • 3 guests

  • 1 bedrooms

Rush & Division, Chicago

Savings Account

Savings Account

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Checking Account

Checking Account

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Grey Marl

Grey Marl

  • 3 guests

  • 1 bedrooms

Near North, Chicago

Solo Bird

Solo Bird

  • 2 guests

  • 1 bedrooms

Near North, Chicago

Skyscraper

Skyscraper

  • 3 guests

  • 1 bedrooms

Near North, Chicago

On Cloud Nine

On Cloud Nine

  • 2 guests

  • 1 bedrooms

Near North, Chicago

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Check upcoming rates & availability for New Eastside Vacation Rentals


Frequently asked questions

Take a look at our collection of luxury Vacation Rentals in New Eastside. All of the homes you'll find on Plum Guide come fully furnished with all linen, the best-equipped kitchens, and essential bathroom toiletries included. Each home is systematically reviewed before becoming part of our collection, so you can book your stay with total confidence. And if you require any assistance in finding the perfect New Eastside Vacation Rentals for you, get in touch with our team of friendly experts, on hand to help with whatever you need.

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